NP-MRD: Showing NP-Card for (1s,4s,5r,6r,9s,10r,11s,12r,14r)-4,5,6-trihydroxy-7,11-bis(hydroxymethyl)-3,11,14-trimethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one (NP0152380)

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Record Information

Version

2.0

Created at

2022-09-02 08:50:48 UTC

Updated at

2022-09-02 08:50:48 UTC

NP-MRD ID

NP0152380

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4s,5r,6r,9s,10r,11s,12r,14r)-4,5,6-trihydroxy-7,11-bis(hydroxymethyl)-3,11,14-trimethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one

Description

16-Hydroxyingenol belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane. (1s,4s,5r,6r,9s,10r,11s,12r,14r)-4,5,6-trihydroxy-7,11-bis(hydroxymethyl)-3,11,14-trimethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one is found in Euphorbia ingens. (1s,4s,5r,6r,9s,10r,11s,12r,14r)-4,5,6-trihydroxy-7,11-bis(hydroxymethyl)-3,11,14-trimethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one was first documented in 2020 (PMID: 32643405). Based on a literature review very few articles have been published on 16-Hydroxyingenol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022210502D          

 26 29  0  0  1  0            999 V2000
    0.3613   -0.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9956   -0.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995   -0.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3190   -1.1719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9381   -1.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -0.9524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5764   -2.0847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2647   -2.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4725   -3.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3711   -3.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6114   -4.2935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7697   -2.6832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0519   -3.0897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7271   -1.8217    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0550   -2.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9496   -1.5083    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2533   -1.9508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2279   -1.5430    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2412   -0.7181    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5885   -0.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7723   -0.4094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2661    0.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9489   -1.1421    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6323   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6171   -1.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3703   -1.2895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  2  0  0  0  0
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  1  0  0  0
  7 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  1  6  0  0  0
 19 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  6  0  0  0
 25 26  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    3.8455   -2.0821   -2.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7083   -1.4809   -1.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4441   -1.3648   -1.6376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7002   -0.7345   -0.5904 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2028    0.3601   -0.9610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4055    0.7361   -2.0574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9567    1.0909    0.1526 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2553    2.3374    0.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0814    2.3971    0.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    3.7242    0.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5310    4.5902    1.0694 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0713    1.3373   -0.0316 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2776    1.6789    0.5496 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6876   -0.0560    0.3635 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2975   -0.1722    1.6746 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9172   -0.9233    0.0850 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1145   -1.8566    1.0699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3182    0.8975   -0.2934 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4844   -0.5265   -0.6790 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6795   -1.6123   -0.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2657   -1.6620    0.1478 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3085   -3.0552    0.0222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3655    0.1359    0.4130 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2163   -0.3404    1.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8271    0.3900    0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8230    1.2294   -1.0635 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4665   -2.7430   -2.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4686   -1.3123   -2.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4039   -2.7339   -1.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0778   -1.7097   -2.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8877    0.5614    1.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8022    3.2441    0.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2600    3.6197    1.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1643    4.1812   -0.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3790    5.2517    0.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1494    1.3581   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7150    2.3623   -0.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625    0.5267    2.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -0.3026    0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8967   -1.6478    1.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6990    1.6774   -0.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0498   -0.6423   -1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2161   -2.1369    0.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7600   -2.4523   -1.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1296   -1.3846    1.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8291   -3.3650    0.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5689   -3.7411   -0.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9239   -3.1702   -0.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2144   -0.6170    2.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8667   -1.2425    1.9683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5478    0.5022    2.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2911   -0.6096   -0.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3936    0.7920    0.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5829    0.6959   -1.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 16  2  1  0
  2  1  1  0
  2  3  2  0
  4  3  1  6
  4  5  1  0
  5  6  2  0
 18 23  1  0
 23 24  1  1
 23 25  1  0
 25 26  1  0
  4 21  1  0
 23 19  1  0
  5  7  1  0
  4 14  1  0
 22 46  1  0
 22 47  1  0
 22 48  1  0
 21 45  1  1
 20 43  1  0
 20 44  1  0
 19 42  1  6
 18 41  1  6
  7 31  1  1
  8 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  6
 13 37  1  0
 15 38  1  0
 16 39  1  6
 17 40  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
 24 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 25 53  1  0
 26 54  1  0
M  END


  Mrv1652309022210502D          

 26 29  0  0  1  0            999 V2000
    0.3613   -0.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9956   -0.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995   -0.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3190   -1.1719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9381   -1.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -0.9524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5764   -2.0847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2647   -2.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4725   -3.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3711   -3.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6114   -4.2935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7697   -2.6832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0519   -3.0897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7271   -1.8217    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0550   -2.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9496   -1.5083    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2533   -1.9508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2279   -1.5430    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2412   -0.7181    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5885   -0.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7723   -0.4094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2661    0.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9489   -1.1421    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6323   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6171   -1.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3703   -1.2895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  2  0  0  0  0
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  1  0  0  0
  7 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  1  6  0  0  0
 19 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  6  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0152380

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H]2[C@H]([C@@H]3C=C(CO)[C@@H](O)[C@]4(O)[C@@H](O)C(C)=C[C@@]14C3=O)[C@@]2(C)CO

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O6/c1-9-6-19-10(2)4-13-14(18(13,3)8-22)12(17(19)25)5-11(7-21)16(24)20(19,26)15(9)23/h5-6,10,12-16,21-24,26H,4,7-8H2,1-3H3/t10-,12+,13-,14+,15+,16-,18+,19+,20-/m1/s1

> <INCHI_KEY>
AZXGMVPOGCUUJQ-IJGBQYEASA-N

> <FORMULA>
C20H28O6

> <MOLECULAR_WEIGHT>
364.438

> <EXACT_MASS>
364.188588622

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.10274472225987

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4S,5R,6R,9S,10R,11S,12R,14R)-4,5,6-trihydroxy-7,11-bis(hydroxymethyl)-3,11,14-trimethyltetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-15-one

> <ALOGPS_LOGP>
0.05

> <JCHEM_LOGP>
-0.9881031303333327

> <ALOGPS_LOGS>
-1.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.826070098768579

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.883732768731592

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4107826054319563

> <JCHEM_POLAR_SURFACE_AREA>
118.22000000000001

> <JCHEM_REFRACTIVITY>
95.80159999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.52e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5R,6R,9S,10R,11S,12R,14R)-4,5,6-trihydroxy-7,11-bis(hydroxymethyl)-3,11,14-trimethyltetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       0.675  -0.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.858  -1.275   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.359  -0.910   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.329  -2.188   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.484  -3.024   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.389  -1.778   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.676  -3.891   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.094  -5.357   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.615  -5.886   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.426  -7.414   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.008  -8.015   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.304  -5.009   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.964  -5.768   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.224  -3.400   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.969  -4.293   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.773  -2.816   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.473  -3.642   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.892  -2.880   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.917  -1.341   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.698  -0.315   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.175  -0.764   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.230   0.452   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.238  -2.132   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.514  -1.269   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.485  -3.035   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.891  -2.407   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14   21                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    4   15   16                                             
CONECT   15   14                                                            
CONECT   16   14    2   17                                                  
CONECT   17   16                                                            
CONECT   18    7   19   23                                                  
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20    4   22                                                  
CONECT   22   21                                                            
CONECT   23   19   18   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₆

Average Mass

364.4380 Da

Monoisotopic Mass

364.18859 Da

IUPAC Name

(1S,4S,5R,6R,9S,10R,11S,12R,14R)-4,5,6-trihydroxy-7,11-bis(hydroxymethyl)-3,11,14-trimethyltetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-15-one

Traditional Name

(1S,4S,5R,6R,9S,10R,11S,12R,14R)-4,5,6-trihydroxy-7,11-bis(hydroxymethyl)-3,11,14-trimethyltetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-15-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H]2[C@H]([C@@H]3C=C(CO)[C@@H](O)[C@]4(O)[C@@H](O)C(C)=C[C@@]14C3=O)[C@@]2(C)CO

InChI Identifier

InChI=1S/C20H28O6/c1-9-6-19-10(2)4-13-14(18(13,3)8-22)12(17(19)25)5-11(7-21)16(24)20(19,26)15(9)23/h5-6,10,12-16,21-24,26H,4,7-8H2,1-3H3/t10-,12+,13-,14+,15+,16-,18+,19+,20-/m1/s1

InChI Key

AZXGMVPOGCUUJQ-IJGBQYEASA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Euphorbia ingens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Tigliane and ingenane diterpenoids

Alternative Parents

Substituents

Ingenane diterpenoid
Tertiary alcohol
Secondary alcohol
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.05	ALOGPS
logP	-0.99	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	11.88	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	118.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.8 m³·mol⁻¹	ChemAxon
Polarizability	38.1 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119057278

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tran TN, Sichaem J, Nguyen VK, Nguyen HH, Cao TT, Nguyen TP, Vo VG, Niamnont N, Nguyen NH, Duong TH: New diterpenoids from the stems of Euphorbia antiquorum growing in Vietnam. Nat Prod Res. 2020 Jul 9:1-8. doi: 10.1080/14786419.2020.1789634. [PubMed:32643405 ]
LOTUS database [Link]

Showing NP-Card for (1s,4s,5r,6r,9s,10r,11s,12r,14r)-4,5,6-trihydroxy-7,11-bis(hydroxymethyl)-3,11,14-trimethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one (NP0152380)

MOL for NP0152380 ((1s,4s,5r,6r,9s,10r,11s,12r,14r)-4,5,6-trihydroxy-7,11-bis(hydroxymethyl)-3,11,14-trimethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)

3D MOL for NP0152380 ((1s,4s,5r,6r,9s,10r,11s,12r,14r)-4,5,6-trihydroxy-7,11-bis(hydroxymethyl)-3,11,14-trimethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)

3D SDF for NP0152380 ((1s,4s,5r,6r,9s,10r,11s,12r,14r)-4,5,6-trihydroxy-7,11-bis(hydroxymethyl)-3,11,14-trimethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)

3D-SDF for NP0152380 ((1s,4s,5r,6r,9s,10r,11s,12r,14r)-4,5,6-trihydroxy-7,11-bis(hydroxymethyl)-3,11,14-trimethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)

PDB for NP0152380 ((1s,4s,5r,6r,9s,10r,11s,12r,14r)-4,5,6-trihydroxy-7,11-bis(hydroxymethyl)-3,11,14-trimethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)

3D PDB for NP0152380 ((1s,4s,5r,6r,9s,10r,11s,12r,14r)-4,5,6-trihydroxy-7,11-bis(hydroxymethyl)-3,11,14-trimethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)

SMILES for NP0152380 ((1s,4s,5r,6r,9s,10r,11s,12r,14r)-4,5,6-trihydroxy-7,11-bis(hydroxymethyl)-3,11,14-trimethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)

INCHI for NP0152380 ((1s,4s,5r,6r,9s,10r,11s,12r,14r)-4,5,6-trihydroxy-7,11-bis(hydroxymethyl)-3,11,14-trimethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)

Structure for NP0152380 ((1s,4s,5r,6r,9s,10r,11s,12r,14r)-4,5,6-trihydroxy-7,11-bis(hydroxymethyl)-3,11,14-trimethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)

3D Structure for NP0152380 ((1s,4s,5r,6r,9s,10r,11s,12r,14r)-4,5,6-trihydroxy-7,11-bis(hydroxymethyl)-3,11,14-trimethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-15-one)